Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

被引：4

作者：

Prasad Nambiar, Anjana ^{[1
]}

Nag, Probal ^{[1
]}

Mariam Ipe, Ruth ^{[1
]}

Reddy Vennapusa, Sivaranjana ^{[1
]}

Gokulnath, Sabapathi ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res, Dept Chem, Thiruvananthapuram 695551, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 30期

关键词：

Chirality; Circularly Polarized Luminescence; Conformation; Helical Enantiomers; Porphyrinoids; AROMATICITY; CHIRALITY;

D O I：

10.1002/anie.202306566

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the synthesis of anthracene-containing twisted cyclo[2]dipyrrin 1 by utilizing a non-planar building block, 1,5-dipyrrylanthracene (1,5-DPA). The non-planar nature of the macrocycle enhanced the solubility and helped in structural characterization. Macrocycle 1 adopts a twisted 'figure of eight' conformation stabilized by strong intramolecular H-bonding interactions and exists as a pair of helical enantiomers, as revealed by X-ray crystallographic analysis. More importantly, the sterically locked structure enabled facile optical resolution using chiral HPLC. The (P,P) and (M,M) enantiomers show moderate chiroptical properties, such as absorption dissymmetry factors |g(abs)| in the order of 10(-3), and luminescence dissymmetry factors |g(lum)| of 3.8x10(-3) and 2.9x10(-3) at 702 nm, respectively.

引用

页数：5

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